Windy City Rooftop Bars

Chicagoans affectionately call the summer months "rooftop season" and head en masse to the nearest hotel penthouse bar for happy hour. Join the fun and check out one of Travel Savvy's picks for outdoor summer cocktails.

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Photo Credit: The Dec Rooftop Lounge + Bar

The Dec - At The Ritz-Carlton

The Dec bar atop the Ritz-Carlton is an easy Chicago favorite. It's sophisticated and trendy, plus the bar menu includes everything from cocktails to scotches and everything in between. Sip on a Cottontail or Boulevardier, munch on some pretzel bites, and escape from the madness of downtown Chicago.

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Photo Credit: Vertigo Sky Lounge Facebook

Vertigo Sky Lounge - At Dana Hotel & Spa

Vertigo is the perfect place to hit up on a weekday for some happy hour drinks and relaxation after work. But look out - when the weekend rolls around, this lounge turns into a poppin' bar with a DJ and chic vibe. Stop by the rooftop of the Dana Hotel for anything from a chill night to a vivacious soiree.

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Photo Credit: The Terrace

The Terrace - At Trump

The Terrace has breathtaking views, delicious signature cocktails, and top-of-the-line cuisine. Like all Trump bars, patrons splurge on the drinks so they can bask in the swanky scene the brand is known for. Watch fireworks from the rooftop on Wednesdays and Sundays post Memorial Day and enjoy the sights of the Chicago River and Lake Michigan below.

ROOF on theWit

There's never a dull moment at ROOF. This is the 'in' spot for locals all evening, with the after-work crowd mixing in with later partygoers well into the night. Along with a full bar, the specialty menu features punch bowls, champagne magnums, mixed drink pitchers with cute names like Love Your #Selfie, and larger food platters. A perfect spot for large groups and good times.